A new lignan glycoside from Juniperus rigida

Archives of Pharmacal Research

Volumn 34, Issue 12, 2011, Pages 2043-2049

  Woo, Kyeong Wan ^a   Choi, Sang Un ^b   Park, Jong Cheol ^c   Lee, Kang Ro ^a  

^a Sungkyunkwan University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

^c Sunchon National University   (South Korea)

Author keywords

Cupressaceae; Cytotoxicity; Juniperus rigida; Labdane diterpene; Lignan glycoside

Indexed keywords

13 EPI CUPRESSIC ACID; 13 EPI TORULOSAL; 2,3 DIHYDRO 7 METHOXY 2 (4' HYDROXY 3' METHOXYPHENYL) 3 HYDROXYMETHYL 5 BENZOFURANPROPANOL 4' O (3 O METHYL) ALPHA LEVO RHAMNOPYRANOSIDE; DEOXYPODOPHYLLOTOXIN; ICARISIDE E4; IMBRICATORIC ACID; ISOCUPRESSIC ACID; JUNIPERIGISIDE; LIGNAN; NORTRACHELOGENIN; SAVININ; SULFORHODAMINE B; THUJASTANDIN; TRANS COMMUNIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; IN VITRO STUDY; JUNIPER BERRIES; JUNIPERUS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; PLANT STEM;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; GLYCOSIDES; HUMANS; JUNIPERUS; LIGNANS; PLANT EXTRACTS; PLANT LEAVES; PLANT STEMS;

EID: 84863153649     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-011-1206-9     Document Type: Article

References (28)

1. Achenbach, H., Waibel, R., and Addae-mensah, I., Lignans and other constituents from Carissa edulis. Phytochemistry, 22, 749-753 (1983).
2. Chang, S.-T., Wang, D. S.-Y., Wu, C.-L., Shaiah, S.-G., Kuo, Y.-H., and Chang, C.-J., Cytotoxicity of extractive from Taiwania cryptomerioides heartwood. Phytochemistry, 55, 227-232 (2000).
3. Chen, J. J., Hung. H. C., Sung, P. J., Chen, I. S., and Kuo, W. L., Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis. Phytochemistry, 72, 523-532 (2011).
4. Fukuyama, Y., Nakahara, M., Minami, H., and Kodama, M., Two new benzofuran-type lignans from the wood of Viburnum awabuki. Chem. Pharm. Bull. (Tokyo), 44, 1418-1420 (1996). (Pubitemid 26256521)
5. Gardner, D. R., Molyneux, R. J., James, L. F., Panter, K. E., and Stegelmeier, B. L., Ponderosa pine needle-induced abortion in beef cattle: identification of isocupressic acid as the principal active compound. J. Agric. Food Chem., 42, 756-761 (1994).
6. Gordien, A. Y., Gray, A. I., Franzblau, S. G., and Seidel, V., Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae). J. Ethnopharmacol., 126, 500-505 (2009).
7. Hanari, N., Yamamoto, H., and Kuroda, K. I., Comparison of terpenes in extracts from the resin and the bark of the resinous stem canker of Chamaecyparis obtusa and Thujopsis dolabrata var. hondae. J. Wood Sci., 48, 56-63 (2002). (Pubitemid 37292838)
8. Ito, C., Matsui, T., Wu, T. S., and Furukawa, H., Isolation of 6,7-demethylenedesoxypodophyllotoxin from Hernandia ovigera. Chem. Pharm. Bull. (Tokyo), 40, 1318-1321 (1992).
9. Kato, A., Hashimoto, Y., and Kidokoro, M., (+)-Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica. J. Nat. Prod., 42, 159-162 (1979).
10. Kim, T. H., Ito, H., Hayashi, K., Hasegawa, T., Machiguchi, T., and Yoshida T., Aromatic constituents from the heartwood of Santalum album L. Chem. Pharm. Bull. (Tokyo), 53, 641-644 (2005). (Pubitemid 40880256)
11. Kuo, Y. H. and Yu, M. T., Three labdane-type diterpenes from the bark of Juniperus formosana HAY. var. concolor HAY. Chem.Pharm. Bull. (Tokyo), 44, 1242-1244 (1996).
12. Lee, T. B., Coloured Flora of Korea. Hyang-Moon Publishing Co, Seoul, p. 150, (2003).
13. Lee, Y. S., Kim, J. H., Kim, H. J., Sohn, E. J., Kim, C. S., Jeong, I. H., Jo, K. H., Kim, J. H., and Kim, J. S., Anti-lipase and lipolytic activities of EtOH extract from Juniperus rigida. Kor. J. Pharmacogn., 41, 216-220 (2010).
14. Li, S., Iliefski, T., Lundquist, K., and Wallis, A. F. A., Reassignment of relative stereochemistry at C-7 and C-8 in arylcoumaran neolignans. Phytochemistry, 46, 929-934 (1997). (Pubitemid 27488302)
15. Liu, C. M., Zhou, H. B., and Zhang, W. D., Terpenoids from stems and leaves of Cupressus gigantea. Chin. J. Nat. Med., 8, 405-410 (2010).
16. Matsuda, N., Sato, H., Yaoita, Y., and Kikuchi, M., Isolation and absolute structures of the neolignan glycosides with the enantiomeric aglycones from the leaves of Viburnum awabuki K. KOCH. Chem. Pharm. Bull. (Tokyo), 44, 1122-1123 (1996). (Pubitemid 26193464)
17. Miyase, T., Uedo, A., Takizawa, N., Kobayashi, H., and Oguchi, H., Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry, 28, 3483-3485 (1989).
18. Murakami, K., The structure of thujastandin, a new lignan from Thuja standishii (GORD.) CARR. Mokuzai Gakkaishi, 13, 265 (1967).
19. Nakanishi, T., Iida, N., Inatomi, Y., Murata, H., Inada, A., Murata, J., Lang, F. A., Iinuma, M., and Tanaka, T., Neolignan and flavonoid glycosides in Juniperus communis var, depressa. Phytochemistry, 65, 207-213 (2004). (Pubitemid 38147358)
20. Nishibe, S., Chiba, M., Sakushima, A., Hisada, S., Yamanouchi, S., Takido, M., Sankawa, U., and Sakakibara, A., Introduction of an alcoholic hydroxyl group into 2,3-dibenzylbutyrolactone lignans with oxidizing agents and carbon-13 nuclear magnetic resonance spectra of the oxidation products. Chem. Pharm. Bull. (Tokyo), 28, 850-860 (1980).
21. Pan, H. and Lundgren, L. N., Phenolic extractives from root bark of Picea abies. Phytochemistry, 39, 1423-1428 (1995).
22. Skehan, P., Storeng, R., Scudiero, D., Monks, A., Mcmahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicty assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990). (Pubitemid 20213250)
23. Su, W. C., Fang, J. M., and Cheng, Y. S., Labdanes from Cryptomeria japonica. Phytochemisry, 37, 1109-1114 (1994).
24. Takaku, N., Choi, D. H., Mikame, K., Okunishi, T., Suzuki, S., Ohashi, H., Umezawa, T., and Shimada, M., Lignans of Chamaecyparis obtusa. J. Wood Sci., 47, 476-482 (2001).
25. Tomita, B. and Hirose, Y., Allo-cedrol : a new tricarbocyclic sesquiterpene alcohol. Phytochemistry, 12, 1409-1414 (1973).
26. Yanagawa, T. and Hirose, Y., Terpenoids. xxix. diterpenes in the wood of Juniperus rigida. Mokuzai Gakkaishi, 17, 306-310 (1971).
27. Yeo, H. S., Chin, Y. W., Park, S. Y., and Kim, J. W., Lignans of Rosa multiflora roots. Arch. Pharm. Res., 27, 287-290 (2004).
28. Yuen, M. S. M., Xue, F., Mak, T. C. W., and Wong, H. N. C., On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton. Tetrahedron, 54, 12429-12444 (1998). (Pubitemid 28552685)